(5aR,10bR)-1,3,9-trihydroxy-8-methoxy-5a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-10bH-indeno[2,1-b][1]benzofuran-6-one

Details

• Internal ID: 862500a1-9010-49b4-bfc0-c2b87af91710
• Taxonomy: Benzenoids > Indanes > Indanones
• IUPAC Name: (5aR,10bR)-1,3,9-trihydroxy-8-methoxy-5a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-10bH-indeno[2,1-b][1]benzofuran-6-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC34C(C5=CC(=C(C=C5C3=O)OC)O)C6=C(C=C(C=C6O4)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@]34[C@H](C5=CC(=C(C=C5C3=O)OC)O)C6=C(C=C(C=C6O4)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H32O16/c1-8-19(32)21(34)23(36)26(41-8)40-7-16-20(33)22(35)24(37)27(42-16)44-28-18(17-13(31)3-9(29)4-15(17)43-28)10-5-12(30)14(39-2)6-11(10)25(28)38/h3-6,8,16,18-24,26-27,29-37H,7H2,1-2H3/t8-,16+,18+,19-,20+,21+,22-,23+,24+,26+,27-,28+/m0/s1
• InChI Key: DXOKOFWCEQXYQM-DNWFQKTLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₆
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.16903493 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.10
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5384	53.84%
Caco-2	-	0.8989	89.89%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7136	71.36%
OATP2B1 inhibitior	-	0.7176	71.76%
OATP1B1 inhibitior	+	0.8606	86.06%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6101	61.01%
P-glycoprotein inhibitior	-	0.5672	56.72%
P-glycoprotein substrate	+	0.5498	54.98%
CYP3A4 substrate	+	0.6769	67.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8348	83.48%
CYP3A4 inhibition	-	0.7147	71.47%
CYP2C9 inhibition	-	0.8305	83.05%
CYP2C19 inhibition	-	0.7277	72.77%
CYP2D6 inhibition	-	0.8534	85.34%
CYP1A2 inhibition	-	0.8416	84.16%
CYP2C8 inhibition	+	0.6318	63.18%
CYP inhibitory promiscuity	-	0.6322	63.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5900	59.00%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9049	90.49%
Skin irritation	-	0.8147	81.47%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.5555	55.55%
Human Ether-a-go-go-Related Gene inhibition	-	0.4381	43.81%
Micronuclear	+	0.7092	70.92%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8703	87.03%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7971	79.71%
Acute Oral Toxicity (c)	III	0.6857	68.57%
Estrogen receptor binding	+	0.8244	82.44%
Androgen receptor binding	+	0.6117	61.17%
Thyroid receptor binding	+	0.5853	58.53%
Glucocorticoid receptor binding	+	0.6931	69.31%
Aromatase binding	+	0.6040	60.40%
PPAR gamma	+	0.7073	70.73%
Honey bee toxicity	-	0.6980	69.80%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8603	86.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.45%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.74%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.31%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.39%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.97%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.17%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.09%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.27%	85.14%
CHEMBL4208	P20618	Proteasome component C5	89.50%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.45%	97.36%
CHEMBL1937	Q92769	Histone deacetylase 2	88.15%	94.75%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.96%	85.31%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.95%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.69%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.41%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.19%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.28%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.95%	95.89%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.76%	94.42%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.45%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.92%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	80.44%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.28%	95.89%

Plants that contains it

• Kaempferia parviflora
• Ligularia veitchiana

Cross-Links

• PubChem: 162898565
• LOTUS: LTS0274957
• wikiData: Q105248508